Simon Rohrbach, Co-Founder and CEO at Plain, reflects on the four-year journey since he and Matt Vagni started their venture. As a company focused on customer support for B2B businesses, Plain has had its share of struggles and successes. In his post, Simon Rohrbach shares valuable insights that go beyond the obvious advice for startups. Instead, he dives into the less obvious lessons that have shaped Plain’s evolution, offering key takeaways for anyone building a business in an ever-changing world.
Simon Rohrbach begins by reflecting on the early days of Plain, which he describes as “wandering in the desert.” For the first three years, Plain didn’t see much traction, and by traditional metrics, the company could have been labeled a failure. However, Simon Rohrbach stresses that success is not always immediate or linear. His first lesson is simple yet profound: “If you’re not winning, just don’t lose.” Sometimes, the key to success is simply staying in the game long enough for opportunities to emerge. The early years of Plain were about building a solid foundation, iterating on ideas, and holding steady until the moment arrived when things finally started to click.
This resonates with the experiences of many entrepreneurs who may feel discouraged during the initial stages of building a company. Simon Rohrbach’s words serve as a reminder that persistence is often the key to eventual success. Staying focused on the long-term vision, even when progress feels slow, is crucial. “Keeping at it, recognizing when the moment arrives, and seizing it is what matters,” says Simon Rohrbach. The company’s recent growth shows that what may have seemed like a failure initially can quickly transform into a success story when the right conditions align.
Another key lesson Simon Rohrbach shares is the importance of becoming “somewhat good” at various aspects of running a business. In the early stages of a startup, founders often have to wear many hats, even if they’re not experts in every area. Simon Rohrbach admits that he wasn’t the best manager, salesperson, engineer, or designer. However, the early days of Plain required him to get good at tackling the company’s biggest problems, no matter what they were. “One day, that will be closing an important customer, and the next day, it will be hiring,” he explains. The ability to learn, adapt, and become proficient enough in different roles is essential to keeping the business moving forward.
Simon Rohrbach emphasizes the importance of enjoying the process of learning and improving. It’s not about being perfect; it’s about getting better each day. His approach speaks to the reality that early-stage founders must be agile, willing to step outside their comfort zones, and constantly evolving. By embracing the journey of “going from incompetent to a little less incompetent every day,” Simon Rohrbach highlights the mindset necessary to navigate the complexities of building a company from the ground up.
A third valuable lesson from Simon Rohrbach’s experience is the importance of developing clear swim lanes with co-founders. As the company grows, it becomes less feasible to have opinions on every detail of how things should be done. There comes a point when founders must trust each other’s judgment and focus on outcomes rather than processes. Simon Rohrbach acknowledges that there will be no “right” answer in many situations, and wasting time debating minor details is counterproductive. Instead, he advises working with a coach, as he and Matt Vagni did, to establish clear areas of responsibility and hold each other accountable for results.
This approach fosters a culture of trust and collaboration, which is vital for scaling a business. Simon Rohrbach’s advice to entrepreneurs is to find ways to delegate, streamline decision-making, and empower team members to take ownership of their roles. This not only improves efficiency but also helps co-founders avoid burnout by ensuring they aren’t bogged down in unnecessary debates over minutiae.
An equally important lesson that Simon Rohrbach shares is the need for an outlet outside of work. For him, that outlet has become long-distance running. It serves as a way to decompress and process the challenges of running a startup. “I get to run during the week after a long day, and I’m always excited about my long run during the weekend,” says Simon Rohrbach. He credits running with improving his mental and physical health, making him happier and more energized. This balance between work and personal life has fundamentally changed his relationship with work, allowing him to approach each day with a refreshed perspective.
Simon Rohrbach’s emphasis on finding a healthy outlet underscores the importance of self-care for founders. Building a company can be all-consuming, but it’s crucial to have an activity that helps you recharge and maintain a clear mind. Whether it’s running, meditation, or spending time with loved ones, finding that balance can make a significant difference in sustaining energy and focus over the long term.
As Simon Rohrbach looks ahead to the next four years at Plain, he expresses excitement and optimism about the journey that lies ahead. He’s proud of the accomplishments of the team, the trust of investors, and the relationships built with customers. His post ends with a simple yet poignant reminder: take photos of the big moments. These snapshots—whether physical or metaphorical—serve as important reminders of how far you’ve come, even when the journey feels like an endless grind.
Simon Rohrbach’s reflections on four years of building Plain offer valuable lessons for any entrepreneur. From the importance of persistence to the value of learning on the job, developing trust with co-founders, and maintaining a healthy work-life balance, Rohrbach’s insights resonate with the realities of startup life. His story is one of resilience, adaptability, and the willingness to embrace the ups and downs of building something meaningful. As Simon Rohrbach and the Plain team continue their journey, they offer a roadmap for success in the ever-evolving world of B2B customer support.
